Welcome back fellow investopreneurs!

🎉 350 Issues Strong → Thank You!

Before we dive into today’s newsletter, we just want to pause and say a massive THANK YOU for being here with us.

This week marks our 350th consecutive weekly issue 🥳. What started years ago as a simple “buy and build in public” experiment has turned into one of my absolute favorite things to show up for every single week.

And honestly? That’s because of you.

If it weren’t for the insane open rates we see week after week (90%+ 🤯), I probably would have outsourced this newsletter….or maybe even retired it….long ago.

But every time I pull up the analytics and see thousands of you opening, reading, and engaging… it fills my tank ⛽️ and reminds me why I love writing this.

So from the bottom of my heart: thank you for being part of this journey.

👉 To celebrate, we’re announcing something brand new tomorrow! If you want early access, you can join the waitlist here and get in 1 hour before anyone else.

🎙️ Bootstrapping to Billions Episode 4

This past week I got to sit down with Dom Wells of Onfolio and he gave us an hour plus long masterclass on how he went from being a school teacher → to CEO of a NASDAQ holding company.

What Is a HoldCo?

A holding company—often shortened to HoldCo—is the entrepreneur’s ultimate leverage play. Unlike an operating business, a HoldCo doesn’t exist to sell products, deliver services, or sign up customers. Instead, it exists to own the entities that do those things.

Think of a HoldCo as the umbrella that protects and connects everything underneath. It doesn’t sell lemonade—it owns the lemonade stand, the sugar supplier, and the ice machine. It doesn’t need to be the day-to-day operator, because its job is to organize ownership, mitigate risk, and direct capital.

At its simplest, a HoldCo:

• Owns other companies outright or in part (subsidiaries, equity stakes, or joint ventures).

• Separates risk so a lawsuit, bad debt, or operational issue in one company doesn’t jeopardize the entire portfolio.

• Provides flexibility to redeploy capital and reinvest across businesses.

The best-known examples are giants like Berkshire Hathaway, IAC/InterActiveCorp, and family offices that quietly run dozens of companies behind the scenes. But HoldCos aren’t just for billionaires—they’re for anyone who thinks in terms of equity instead of just income.

And here’s the key shift: a HoldCo isn’t about running one business well. It’s about creating a system of ownership that compounds across many.

Why Create a HoldCo?

The short answer: because every business you build will eventually end.

Markets change. Customer behavior shifts. Competitors catch up. Even if your company survives decades, you won’t always want to run it. If your wealth and identity are tied to one single operating business, you’re exposed to a level of risk that no sophisticated investor would accept.

A HoldCo solves that problem.

1. Diversification Without Distraction

Most founders get stuck running “the one business.” But when you’re an owner through a HoldCo, you can hold multiple bets at once. A construction company can fund a real estate development arm. A SaaS platform can spin off a consulting agency. A seasonal business can be balanced with one that thrives year-round.

This diversification gives you resilience. If one company is down, the HoldCo’s portfolio isn’t wiped out.

2. Tax and Legal Protection

When you silo ownership under a HoldCo, you protect both the businesses and yourself. One lawsuit in an operating company doesn’t pierce into your personal assets—or into your other companies. Many entrepreneurs don’t realize until it’s too late that by mixing entities or keeping everything under one roof, they’ve concentrated risk instead of reducing it.

A HoldCo acts like fire doors in a building: it contains the blaze.

3. Capital Allocation and Leverage

Here’s where the real magic happens: a HoldCo lets you move money like the big players do. Profits from one company can be upstreamed to the HoldCo, then redeployed into another. You’re no longer relying on a single balance sheet—you’re playing across multiple.

This is how private equity firms build empires. They don’t just make money; they use their structures to multiply money.

4. Generational Wealth Creation

If you think in terms of one business, you’ll likely sell it one day and take a check. If you think in terms of a HoldCo, you’ll build a machine that outlives you. Instead of one exit, you create an ongoing pipeline of exits, acquisitions, and reinvestments.

It’s the difference between being a business owner and being a true wealth architect.

How to Create a HoldCo

On paper, setting up a holding company looks simple: you create a parent entity, and that entity owns your operating companies. In practice, the way you structure it can determine how much flexibility, protection, and leverage you unlock down the road.

Step 1: Form the Parent Entity

At its core, a HoldCo is just a legal entity. Most founders will choose either an LLC or a C-Corp depending on their goals:

• LLC HoldCo → flexible, tax-efficient, great for small groups of owners or family wealth.

• C-Corp HoldCo → built for scale, outside investors, and raising institutional capital.

The important part isn’t which you pick—it’s that you create a separate parent entity that will eventually sit above your operating businesses.

Step 2: Transfer Ownership

Once the HoldCo exists, you restructure ownership so that the parent company owns your subsidiaries. That could look like:

• Assigning your shares in an existing business to the HoldCo.

• Acquiring new businesses under the HoldCo from day one.

• Rolling multiple existing businesses under one roof for unified ownership.

This move might feel like “paperwork,” but it’s a strategic reset. You’re no longer “the business owner.” You’re the owner of the company that owns businesses.

Step 3: Establish Separation and Systems

A true HoldCo doesn’t run day-to-day operations. Each subsidiary has its own:

• Bank accounts

• P&L

• Team and leadership

• Operating agreements

The HoldCo oversees performance, allocates capital, and manages risk—but it doesn’t sell lemonade. The lemonade stand does.

Step 4: Formalize Governance

Even if you’re a solo founder, treat your HoldCo like an investment firm. Hold quarterly reviews. Document how decisions get made. Track how capital moves in and out. By institutionalizing your HoldCo from the start, you create a structure that can scale with acquisitions, partners, or even outside investors later.

The Bootstrapper’s Way vs. The Investor’s Way

• The Bootstrapper’s Way: You don’t need millions to start. If you own a single business today, you can form a HoldCo tomorrow and transfer that business under it. From there, you reinvest profits into a second business, side project, or even passive asset like real estate.

• The Investor’s Way: Raise capital at the HoldCo level, acquire multiple subsidiaries at once, and manage them like a private equity fund.

Both paths are valid. The difference is whether you’re starting with sweat equity or financial capital.

How to Capitalize a HoldCo

A HoldCo is only as strong as the capital it commands. The magic isn’t just in owning multiple businesses—it’s in having the flexibility to fuel them, move money between them, and multiply equity across the portfolio.

Here are the primary ways to capitalize a HoldCo, each with its own tradeoffs:

1. Operating Profits (The Bootstrapper’s Fuel)

The simplest way to capitalize your HoldCo is to flow profits upstream from your operating businesses.

• Subsidiaries send dividends or distributions to the HoldCo.

• The HoldCo banks that cash and redeploys it into new ventures, acquisitions, or reserves.

Pros: No outside investors, no debt obligations, full control.
Cons: Growth is constrained by the pace of your operating businesses.

This is how most Investopreneurs start—a single profitable business acts as the seed engine for the HoldCo.

2. Debt (The Multiplier)

HoldCos can borrow money, just like operating companies. The difference is flexibility. A HoldCo loan can be spread across multiple businesses or used to acquire new subsidiaries.

• Credit lines, term loans, or mezzanine debt at the HoldCo level.

• Often secured by the value of the portfolio.

Pros: Non-dilutive. Lets you scale faster.
Cons: Increases risk—if you over-leverage, one bad year across subsidiaries can create strain.

Sophisticated HoldCos know how to use debt strategically: not to survive, but to accelerate.

3. Equity Partners (The Outside Capital Path)

Instead of raising money for one business, you can raise money at the HoldCo level and let investors share in the whole portfolio.

• Family offices, PE firms, or strategic partners may buy into the HoldCo.

• Great for entrepreneurs who want to move from “owner-operator” to true capital allocator.

Pros: Big checks, validation, access to networks.
Cons: Dilution, governance, reporting obligations.

This is the professional investor’s path—and it’s why many HoldCos start looking more like mini private equity firms over time.

4. Exits (The Flywheel)

Every time you sell a business, you create a capitalization event for your HoldCo. Instead of cashing out personally, you roll those proceeds into the HoldCo.

• Sell one company → seed three more.

• Use exits as liquidity events to scale the portfolio instead of resetting to zero.

Pros: Turns one-time wins into compounding equity.
Cons: Requires discipline—many founders sell and spend instead of reinvesting.

This is the long-term game. The HoldCo becomes a compounding machine fueled by exits, reinvestments, and redeployments.

Putting It Together

Most Investopreneurs use a stacked approach: start with operating profits, layer in some debt, roll in proceeds from exits, and eventually attract outside equity once the portfolio is big enough to justify it.

The point isn’t which path you choose—it’s that with a HoldCo, you have options. You’re not stuck inside one company’s cash flow. You’re free to move money like an investor, not just earn it like an operator.

Business Operator vs. HoldCo Operator

Running a business and running a holding company are two entirely different games. Both are valuable, but they require different skills, different priorities, and different ways of thinking.

An operator is in the trenches. A HoldCo operator is above the battlefield, deciding which trenches are worth digging in the first place.

The Business Operator Mindset

• Focus: Customers, product, sales, team.

• Time Horizon: Short to medium term (this quarter, this year).

• Primary Question: “How do I grow revenue and keep the business running?”

• Identity: Founder, CEO, manager.

• Skill Set: Execution, leadership, operations, customer obsession.

Operators are essential—they make the wheels turn. But they’re often trapped in the day-to-day, unable to step back and see the bigger equity picture.

The HoldCo Operator Mindset

• Focus: Portfolio performance, capital allocation, risk management.

• Time Horizon: Long term (5–20+ years).

• Primary Question: “Where should I deploy capital for the highest risk-adjusted return?”

• Identity: Investor, owner, capital allocator.

• Skill Set: Strategy, finance, governance, deal-making.

A HoldCo operator doesn’t ask, “How do I grow this business?” Instead, they ask, “Should I even keep this business—or would my capital be better redeployed elsewhere?”

The Shift from Operator to HoldCo Builder

The moment you start thinking like a HoldCo, you stop tying your identity to one business. You recognize that businesses are vehicles, not destinations. You learn to:

• Detach emotionally from one company’s ups and downs.

• See capital as fuel, not a byproduct.

• Build systems that outlive individual ventures.

This shift is uncomfortable at first—it feels like “letting go.” But it’s actually graduating from self-employed to investor-owner.

Side-by-Side Snapshot

Why Investopreneurs Make the Best HoldCo Entrepreneurs

Not every founder is wired to run a HoldCo. Plenty of entrepreneurs are great at starting businesses but struggle once the game shifts from operations to capital allocation. That’s why Investopreneurs—entrepreneurs who think like investors—are uniquely positioned to thrive as HoldCo builders.

The Investopreneur Mindset

An Investopreneur isn’t just building businesses for cash flow. They’re building equity machines. Every decision is framed through the lens of:

• Will this increase my equity?

• Will this reduce my risk?

• Will this compound over time?

That mindset naturally mirrors how the best HoldCos operate. While a traditional founder chases growth at all costs, an Investopreneur chases profitable, sustainable, and transferable growth—the kind that can be rolled up into a portfolio.

Bootstrapper → Investopreneur → HoldCo Builder

Here’s the progression most founders miss:

1. Bootstrapper: Pride-rich, cash-poor. Focused on making the business work.

2. Investopreneur: Learns to measure, manage, and multiply equity, not just revenue.

3. HoldCo Builder: Evolves from operator to allocator—deploying capital across businesses, not just inside one.

When you embrace the Investopreneur identity, you’re already building with a HoldCo lens—even if you only own one business.

Why Investopreneurs Win at HoldCos

1. Equity Discipline: They don’t fall in love with one company; they fall in love with compounding equity.

2. Risk Awareness: They actively identify and mitigate risk—because risk isn’t just a headache, it’s a valuation killer.

3. Capital Allocation Skills: They know when to reinvest in growth, when to automate, when to delegate, and when to exit.

4. Exit Thinking: From day one, they’re building businesses designed to be sellable, transferrable, or scalable.

The Big Difference

The truth is: most entrepreneurs will end up trapped inside their one business forever. Investopreneurs don’t. They build with a portfolio mindset. They graduate into HoldCo operators because it’s the natural extension of the way they’ve always thought—like investors first, entrepreneurs second.

For them, a HoldCo isn’t an advanced structure. It’s simply the inevitable result of doing business the Investopreneur way.

Why Building Like a HoldCo Forces You to Be a Better Entrepreneur Through Each of the Five Exits

The beauty of building like a HoldCo is that it forces discipline. You can’t coast. You can’t just “get by” on sales. To succeed, you must grow through every phase of entrepreneurship with a higher standard. That’s why the HoldCo path naturally aligns with the Five Exits of Ownership.

Exit 1: Exit the Day Job

The first step is leaving your 9–5 and making the business your job. Most entrepreneurs stop here—they trade one paycheck for another.

But if you’re thinking like a HoldCo, you already see this business as an asset in your portfolio, not your identity. From day one, you’re building with the intent to eventually place this business under your HoldCo umbrella.

👉 Lesson: Build with transferability in mind from the start.

Exit 2: Exit the Work

Here, you move from doing the work to building a team. For most founders, this is terrifying. But a HoldCo lens makes it obvious: if you’re still doing the work, you don’t own a business—you own a job.

A HoldCo operator knows that teams and systems are non-negotiable. If a business can’t function without you, it doesn’t belong in your portfolio.

👉 Lesson: Ownership is about leverage, not labor.

Exit 3: Exit the Management

This is where you stop managing people and start building systems. Inside a HoldCo, you don’t want a handful of chaotic businesses you have to babysit—you want a clean, standardized portfolio where every subsidiary runs like a machine.

By Exit 3, you’ve built a system-driven business. That’s the only kind of business a HoldCo can scale.

👉 Lesson: Systems are the bridge from business operator to capital allocator.

Exit 4: Exit the Operations

Now you’re hiring true operators to run the day-to-day. At this point, your job has shifted entirely: you’re not in the weeds, you’re at the table of capital allocation.

Inside a HoldCo, this is the defining skill. Do you know when to double down, when to divest, and when to redeploy? Do you know how to pick and empower the right operators? This stage sharpens you into a strategist.

👉 Lesson: Letting go of control is the gateway to scale.

Exit 5: Exit Active Ownership

This is where your HoldCo fully comes alive. You no longer work in your businesses, or even on them—you simply own them. Your HoldCo becomes a wealth engine, powered by systems, operators, and capital allocation.

And here’s the key: by building like a HoldCo, you didn’t just stumble into Exit 5. You were preparing for it all along.

👉 Lesson: True freedom is ownership without dependency.

The Big Picture

Each exit builds on the last, and each one requires sharper discipline. Entrepreneurs who stop at Exit 1 or 2 may build income, but they rarely build wealth. By contrast, entrepreneurs who adopt the HoldCo mindset from the beginning are forced to grow into better owners at every stage.

Because the HoldCo demands it.
Because equity requires it.
Because freedom depends on it.